Ureidopyrazine Derivatives: Synthesis and Biological Evaluation as Anti-Infectives and Abiotic Elicitors

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10364689" target="_blank" >RIV/00216208:11160/17:10364689 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11150/17:10364689 RIV/00179906:_____/17:10364689

Result on the web

<a href="http://www.mdpi.com/1420-3049/22/10/1797/htm" target="_blank" >http://www.mdpi.com/1420-3049/22/10/1797/htm</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules22101797" target="_blank" >10.3390/molecules22101797</a>

Result language

angličtina

Original language name

Ureidopyrazine Derivatives: Synthesis and Biological Evaluation as Anti-Infectives and Abiotic Elicitors

Original language description

Tuberculosis (TB) caused by Mycobacterium tuberculosis (Mtb) has become a frequently deadly infection due to increasing antimicrobial resistance. This serious issue has driven efforts worldwide to discover new drugs effective against Mtb. One research area is the synthesis and evaluation of pyrazinamide derivatives as potential anti-TB drugs. In this paper we report the synthesis and biological evaluations of a series of ureidopyrazines. Compounds were synthesized by reacting alkyl/aryl isocyanates with aminopyrazine or with propyl 5-aminopyrazine-2-carboxylate. Reactions were performed in pressurized vials using a CEM Discover microwave reactor with a focused field. Purity and chemical structures of products were assessed, and the final compounds were tested in vitro for their antimycobacterial, antibacterial, and antifungal activities. Propyl 5-(3-phenylureido)pyrazine-2-carboxylate (compound 4, MICMtb = 1.56 mu g/mL, 5.19 mu M) and propyl 5-(3-(4-methoxyphenyl)ureido)pyrazine-2-carboxylate (compound 6, MICMtb = 6.25 mu g/mL, 18.91 mu M) had high antimycobacterial activity against Mtb H37Rv with no in vitro cytotoxicity on HepG2 cell line. Therefore 4 and 6 are suitable for further structural modifications that might improve their biological activity and physicochemical properties. Based on the structural similarity to 1-(2-chloropyridin-4-yl)-3-phenylurea, a known plant growth regulator, two selected compounds were evaluated for similar activity as abiotic elicitors.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

30104 - Pharmacology and pharmacy

Project

<a href="/en/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptide Drug Delivery Systems Targeting Macrophages for Antimycobacterial Active Compounds</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

—

Volume of the periodical

22

Issue of the periodical within the volume

10

Country of publishing house

CH - SWITZERLAND

Number of pages

16

Pages from-to

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UT code for WoS article

000414670600216

EID of the result in the Scopus database

2-s2.0-85032885669